


Pretty in Pink

by kisahawklin



Series: The Three Body Problem [9]
Category: Supernatural
Genre: Crossdressing, Insecure Sam, M/M, Multi, Panties, Praise Kink
Language: English
Status: Completed
Published: 2015-05-17
Updated: 2015-05-17
Packaged: 2018-03-31 00:55:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,056
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3958381
Author URL: https://archiveofourown.org/users/kisahawklin/pseuds/kisahawklin
Summary: <blockquote class="userstuff">
              <p>Dean gets Sam a birthday present.</p>
            </blockquote>





	Pretty in Pink

**Author's Note:**

  * For [fierypassionfruit](https://archiveofourown.org/users/fierypassionfruit/gifts).



> So fierypassionfruit prompted me with "praise kink would be perfect for them, maybe one of the boys could wear a pair of panties and the other two could just keep telling him how pretty he is and "what a good boy you are to us" and stuff like that" and then [there was this picture](http://samifeur.tumblr.com/post/86922223011/tfw-lingerie-ruffles-sam-winchester) and then this happened.
> 
> ETA: That link is broken, but it was a magnificently photoshopped Sam based on [this picture](http://soleta.net/kisa/Sam-in-panties.jpg).

It's pink. 

The box had been pink too, with a pink ribbon, and Sam had rolled his eyes at Dean even as he opened it with more than a little enthusiasm. They never get each other birthday presents, and the few presents they have given each other over the years had never been wrapped for real, with straight corners and pretty bows, and okay, maybe the box is pink, but that doesn't mean that Sam appreciates it any less.

Same stares down into the box for a long time. He can feel Dean's nervousness, the way he's fidgeting, doesn't know where to put his hands. Cas is as impassive as ever, watching Sam with curious eyes.

"I just… I thought you might…" 

Sam rolls his eyes. Dean can't even put words to it. Cas turns his head to look at Dean and, as is becoming his habit, voices Dean's thoughts. "We just wanted you to know they do make lingerie in your size." Sam chuckles to see Dean close his eyes and shake his head.

"I thought you'd look nice in them," Dean corrects, giving Cas the side-eye. Cas has been remarkably resourceful at getting Dean to talk – misrepresenting Dean's stuttered thoughts has become one of Cas's best tricks.

Sam looks down into the box again. The panties are all tiny ruffles, pink, with garters attached, and there are pink striped stockings, too. He supposes he should be grateful there aren't heels in the box. He figured there were probably places that sold this sort of thing in his size – it's just that Dean and Cas had wanted to go out to a store and buy something right away. There was no way any store that sold women's lingerie would have anything in his size, and if he's being honest, this has never been his kink. Though seeing Dean and Cas in theirs sure did it for him.

It's only fair, he supposes. He keeps track of everything they've done, a mental list of who likes what, who's tried what, and he supposes, a sort of mental tally of who's the kinkiest. He doesn't think there's actually an answer to that question.

Dean and Cas are both staring at him, and he's going to have to make a decision here. He knows he can push it off just a bit, say "some other time" and bury them somewhere in his stuff, eventually to be thrown away. He knows it's nerves; he's pretty sure he's going to look stupid in these, not hot the way Dean and Cas did, and of course they're pink, which makes him feel even more self-conscious.

"Please, Sammy," Dean murmurs. "You'd look so pretty."

Sam swallows hard and ducks his head. Dean's always a bit stingy with praise, and even more so with this kind of praise, and Sam nods jerkily. He can't help the way his whole soul reaches out for Dean's approval, but it's been that way since before he can remember, and those few words are all it takes to convince him, despite his self-consciousness. 

"C'mon," Dean says. "Cas made up the bondage room."

Sam stops in his tracks. He's willing to do this, but he doesn't want to be tied up. He doesn't know how to tell Dean that, though, because if Dean had something in mind, Sam wants to give it to him, but…

"Don't worry," Cas says, reading everything on Sam's face in the split second he hesitated. "We aren't going to tie you up."

Sam nods, picks up the box, and follows Dean and Cas down the winding hallways to the room with the bed they tied Sam up on for months. They call it the bondage room, even though they haven't tied anybody up in a long time, and the joke has never sat particularly well with Sam.

When they get there, though, it's obvious that preparing the room means a metric fuckton of lit candles. There's no ambient light in any of the rooms, so if they want to see each other, they have to leave the lights on. They've had a couple of hilarious nights where they left it pitch black and laughed themselves sick trying to have sex without being able to see, but mostly they leave the lights on. Sam doesn't know about Dean or Cas, but he's in it for the two of them, and he likes to be able to see them, to appreciate their bodies and see their expressions.

Once he gets a little further into the room, leaving Dean and Cas by the door, he can smell something earthy and sweet – red roses, he realizes, the good kind, that don't smell like an old lady's perfume. There are rose petals everywhere, in a thick carpet on the floor and scattered artfully on the bed. There are dozens of roses in vases, too, and Sam takes in a deep breath, holding it in his lungs to appreciate the scent.

Dean and Cas file out, Cas grabbing for the door. "We'll give you a minute to get ready," Dean says, and Sam can tell he kept the cracks about being a girl and Samantha at bay on purpose. 

The door slams shut and Sam is left in a room that's straight out of a bad romance novel with an outfit that not even a romance heroine would wear. He stares down at the panties for a long time. It could be Dean's idea of a joke, he might laugh at Sam when they come back in, take pictures and use it as blackmail forever… or he might actually say Sam looks nice. Chances are roughly 70/30 that it's all a joke.

Maybe 60/40. Cas doesn't usually go in for Dean's jokes, though Dean might not have clued Cas in. Sam stares and stares, and finally moves when he reruns Dean saying _you'd look so pretty_ over in his mind for the fiftieth time.

He strips slowly, keeping his eye on the panties like they might bite him, and when he's put his clothes in the dresser (far, far away from all the candles), he picks up the panties and holds them in front of himself. They're going to be tight, he can tell, but they should fit.

They're silky on the inside. Sam hadn't been expecting that. The ruffles were a little rough when he passed his hand over them, so he's glad for the thoughtfulness of something comfortable next to his skin. 

He's not sure how he feels about the fact that while they cover his junk decently enough, his ass is hanging out the back. He tries to put away thoughts of impracticality; he's never going to wear something like this on a hunt, so it's not like it matters.

The stockings are tougher. They're long enough for his legs, which is a surprise, but the stripes keep twisting as he pulls them up, and it's taking forever because he knows he has to treat them gently. He can remember Jess complaining loudly about ruining her stockings by pulling hard enough to put a finger through them.

There's a soft knock on the door and it cracks open a little. "Sam?" Cas asks. "Dean thought I should see if you need help."

Sam stops with the stockings and breathes a sigh of relief. "Yeah, Cas, please."

Cas comes in, smiling when he flicks his eyes up and down Sam's body. Embarrassment heats his skin and he's glad for the candles and their forgiving light. 

"I can't get the stockings," Sam says, but before he can even finish, Cas shushes him and knocks Sam's hands away from the stocking that's hanging halfway up his left leg. 

"It's okay," Cas says, kneeling in front of the bed. "May I pull your stockings up?" he asks, and at Sam's nod, he picks up Sam's foot to rest on his thigh and pulls the stocking back down to Sam's ankle.

Sam watches, rapt, as Cas straightens the stocking on his foot, his hands warm and kind and making Sam die inside with the way he always does when he touches Sam like this, with tenderness and care, like Sam is something precious to him. 

Cas smoothes the stocking up Sam's leg, carefully keeping it where it's supposed to be and that's when Sam realizes the stripes are _supposed_ to twist, making him feel like a complete idiot. 

He can't dwell on that too long, though, because as Cas's hands slide up his legs, a corresponding heat crawls up from his belly into his chest, stealing his breath and making him tremble. 

"Will you please stand so I can get these all the way up?" Cas asks, his hands circling Sam's leg just above the knee, warm and firm and Sam stands, hitching a breath in as the ruffles of his panties end up right in front of Cas's face. 

Cas breathes hotly onto him, and Sam's trembling shifts to full on shivering, and it only gets worse as Cas pulls the stocking up the rest of the way, clipping it in front. "Please turn around?" Cas asks, not moving, which means as Sam shuffles to oblige, Cas kisses him on his hip as it grazes his face, and then Cas is staring at his ass, up close and personal.

Cas bites him gently on the swell of his ass not covered by the panties and Sam yelps. He twists around to try and see what Cas is doing, but Cas's forehead is resting on the meat of his butt and he can feel Cas's fingers brush the skin at the back of his thigh as they do their job clipping the stocking into the garter at the back. 

"Beautiful," Cas whispers, and Sam turns around to hide his smile. Cas is the only one that can take compliments well, and Sam's trying to learn how to say an easy "thank you" the way Cas does, but the pride it brings with it feels dangerous.

"Will you please turn around and sit back on the bed?" Cas asks, dropping his hands from Sam's leg. Sam does his best, since Cas still isn't moving, so he ends up with his crotch in Cas's face again, and this time Cas tips forward the inch and a half and presses a kiss to the panties, right above Sam's hipbone.

Sam can feel his heart start to race, so he takes a deep breath, half falling back onto the bed, handing over the second stocking and lifting his other foot so Cas can get to it. 

Turns out that Cas is not as savvy about stockings as Sam had thought, and Sam has to show him the trick of rolling it all up so all he has to do is unroll it up Sam's leg. He silently sends a prayer to Jess, thanking her for his education in many feminine things. 

Once Cas gets it, Sam has to go through the excruciatingly slow roll of the stocking up his leg, Cas's hands gently smoothing it into place and finally attaching the clips. He sits back on his haunches and takes his eyes up Sam's body, grinning when he reaches Sam's face. "Lovely," he says, taking Sam's hand and letting Sam help lift him off his knees. 

Sam ducks his head again, even as he mutters, "Thanks, Cas."

Another soft knock on the door interrupts his thoughts and Dean's head appears around the corner. "Hey, you guys –"

Cas steps to the side, quick and weirdly surreptitious considering he's not actually trying to hide. He must have known – hell, they both knew – that Dean would want to see Sam on his own. Sam's tremors come back, nerves that Dean is just teasing him, that this is a joke and Sam knew that was a possibility going in, but he just wasn't prepared for the way his heart is hammering in his chest, ready to be disappointed when Dean calls him Samantha and snaps a picture.

He's not quite as ready for Dean's quiet, "Sammy," and the wrecked look on his face. 

"Dean didn't think you'd wear it," Cas says in an undertone, and Dean's scowls Cas's direction before turning back to Sam. "You look…" His face is doing something complicated and Sam can't wait to see what adjective Dean plans to end that sentence with.

"You look…" Dean starts again, crossing the room, slowly, his eyes meeting Sam's and then dropping down. "You…"

Sam tries not to be disappointed that Dean's never going to finish, tell him how he looks. The disbelief in his eyes should be enough for Sam, but he's finding he wants more. He needs more. Of course, he doesn't want to ask for it, either, but it's only fair. If he wants Dean to use his words, he has to use his own.

"Tell me, Dean," he says, waiting for Dean to drag his eyes back up to meet his. "Please, I need…" He swallows. "I need to hear it."

Normally Sam can't stand that look in Dean's eyes, that pity for Sam accompanied by the anger at himself for god only knows what, probably because he feels like Sam's brokenness is his fault. Tonight, though, Sam'll take it, if it means Dean will tell him things.

"You look…" Dean starts again, this time reaching a hand out and resting it over Sam's tattoo, drumming his fingers on Sam's clavicle, "…like everything I ever wanted."

Sam can't help the little hitch of breath he gets from that, words Dean can't possibly know the value of. His shaking gets worse, and he lets his head drop forward so his hair falls in front of his face. He's embarrassed, but also flush with pride, pleased to be the thing Dean wants most in the world.

"Oh, Sammy," Dean says, and Sam can hear the way the words are laced with regret. "Don't you know?"

Sam shakes his head just a little, just enough to bring his hair more thoroughly over his face. He wants this, needs it, even, but it might kill him to get it.

"You're perfect, Sammy," Dean coos, taking the step that brings their bodies close together. He stays there for a long moment, leaving his right hand over Sam's heart and tracing a finger down Sam's arm with his left. Dean sinks to his knees, tilts his head back to look Sam in the eye and says, "You look good enough to eat," in a growl that goes straight to Sam's cock.

Dean's gaze moves slowly down Sam's body, and he can feel himself getting hard just from Dean's laser focus on him. The panties aren't actually going to cover him if he gets fully hard, but he doesn't think it'll matter anymore at that point.

"Cas," Dean says, and they both turn to him. He's just put his own clothes in the dresser, the drawer above Sam's, and he turns to smile at them.

"Yes, Dean?"

"Doesn't Sam look pretty?"

Sam can feel his skin flaming hot, blushing in a way that rarely happens to him, and it gets worse when Cas says, "Yes, Dean, but Sam is always beautiful."

"Hmm," Dean says, looking up from Sam's panties to meet Sam's eyes again. "I suppose. But he just looks so good like this. What should we do with him?"

Cas finishes putting his clothes away and comes to join them, his eyes raking up and down Sam. Sam swallows hard. "I think we should worship him."

Dean nods. "All right." He leans forward and presses his face into the ruffles of Sam's panties, his cheek lined up perfectly with Sam's cock. He inhales deeply, humming in pleasure, and Sam's starting to wonder if embarrassment can kill you if it goes on too long.

"Smell so good, Sammy," Dean says, leaning back to place a kiss on each of Sam's thighs in the little strip of exposed flesh between the panties and the stockings. "Be right back."

Dean starts stripping as he walks over to the dresser, and Cas comes back to stand in front of him. "It's a fetching look on you, Sam," Cas says, and Sam can't help grinning at _fetching_ because only Cas.

"What do you want today?" Cas asks, hovering his hand over Sam's chest, asking permission with his eyes.

Sam nods just a little, waiting for Cas's hand to land on his ribs, and says, "I want Dean to fuck me." 

Dean makes a very gratifying noise from over by the dresser, and Cas says, "Of course, Sam."

Cas is staring at Sam's chest, and he knows Cas does that sometimes, just zones out in the middle of things, but he's surprised when Cas says, "Can I put my mouth on you?"

"Yeah, Cas," Sam says, and sucks in a sudden breath when Cas goes straight for his nipple, tongue flicking over it repeatedly. Sam moans.

Dean finally finishes undressing himself and makes his way back to them, putting a hand on the back of Cas's head before leaning down to take Sam's other nipple in his mouth.

"Fuck," Sam says, his hands coming up to their shoulders for something to hold on to. He closes his eyes and lets his arousal wash over him, concentrating on the feel of his cock thickening in the panties, growing and eventually poking out of the top when he's fully hard after a minute or two.

"Gorgeous," Dean says, bending down to lick the tip of Sam's cock. "You look so good, Sammy."

He goes back down to his knees, putting his mouth on the shaft of Sam's cock through the panties, mouthing his way down it to where Sam's balls are caught in the fabric and mouthing those too. "So fucking hot," Dean says, and Sam had thought he couldn't get any harder, but his cock begs to differ, standing at attention. "Yeah," Dean says, moving back to the tip of Sam's cock, "you're so good, Sammy."

Dean's hands come up to the top of the stockings, tracing fingers lightly just under the bands. "Can't wait for you to wrap your legs around me."

Sam can't wait either, and Cas knows that's code for "time to get Sam ready" so he stops playing with Sam's nipples – with a final kiss on the one he'd been licking and sucking so carefully – and climbs on the bed behind Sam. He can feel Cas rest his head in the dip of his spine, his breath hot on Sam's skin. "May I?" he asks, and Sam's almost lost his words, but he manages to grit out, "Yes," and waits for Cas to touch him.

Dean's still working at the front of Sam's panties, outlining Sam's cock with his tongue, swirling it over the exposed head. Sam moans, every time. "Yeah," Dean says, "that's it, Sam, let me know you like it."

"Deeee," Sam moans. He can't think anymore, and Dean and Cas's hands gently stroking him everywhere is tearing him apart. 

"That's a good boy," Dean says, and Sam shivers. "Yeah, you keep letting us know, Sammy, be good and keep making those noises."

Sam moans helplessly, breathless as Cas shifts the material of his panties to get to his hole.

"You need to widen your stance, Sammy, so Cas has room to work."

Sam's eyes had slipped shut at some point, and they open back up sluggishly. He blinks down at Dean for a second, trying to understand what Dean wants from him. Dean traces his hands down the inside of Sam's stockings, stopping at Sam's knees, and pushes outwards, and Sam gets it. He shuffles his feet further apart, rewarded with Dean pouting his lips out to suck on Sam's cockhead. Sam moans again.

"Good, Sammy, that's good. Such a good boy."

Every time Dean says "good boy," Sam shivers. He knows it's not the context he really wants to hear those words in, but it's satisfying nonetheless.

There's a few long minutes while Cas preps him and Dean messes around with his cock, smoothing his hands over the ruffles of the panties, up and down the stockings, and occasionally pressing his hand between Sam's legs to press on his perineum. Sam closes his eyes and keeps breathing, settling in idle while he listens to Dean whisper all the words of praise he's ever wanted and then some. 

At some point, Cas stops what he's doing, shifting back onto the bed, and Dean stands, pressing his body into Sam's and shifting them both back a few inches so Sam's legs hit the bed. His hand presses Sam down and he sits, bringing his legs up, heels dug into the bed. 

"Sammy," Dean says, staring down at him. "You look so gorgeous like that." 

Sam's had enough waiting, though, so he shoves back with his heels, making room for Dean on the bed, and backing himself up almost onto Cas's lap. "Fuck me, Dean," he says, smirking when Dean's eyes darken.

Cas left the condom in easy reach, and while Dean rolls it on, Cas pulls Sam flush against his chest, snaking his arms under Sam's to get his fingers on Sam's nipples. 

Sam breathes out harshly, his cock throbbing in his panties. "Come on, Dean," Sam says, shifting on the bed to try and get some friction from the panties.

"I got you, Sammy," Dean says, crawling onto the bed between Sam's legs and running his hands up Sam's stockings. He traces a finger up Sam's inner thigh, stopping long enough to take some lube and grease himself up before shifting the thin strip of material to the side. He must like what he sees, because he says, "Goddamn, Sammy, that's a pretty sight," before he closes the distance and starts to press in. 

"Fuck, so tight," Dean says, "you feel so good," and presses in another inch. Sam closes his eyes and concentrates on Cas's hands, one tweaking his nipple and the other stroking himself, Cas's knuckles catching on Sam's spine. Or on Dean, pressing in smoothly and mumbling incoherent praise, raw and uncensored. 

When Dean gets all the way in, Sam presses his knees into Dean's sides and locks his ankles behind Dean's back. "Fuck, Sammy," Dean says, "that's hot as fuck, your legs, Sammy, goddamn. So gorgeous."

"Dean," Sam says, using his ankles to pull himself down on Dean's cock. " _Fuck me_ ," and Dean does, though still slow and measured, which is fine with Sam because that's the way he likes it. It's perfect, because the shift of the material over his cock with the way Cas is playing with his nipple means he can probably come like this. He thinks Dean knows that, because he's usually careful about making sure Sam's got a hand on him, but he doesn't seem inclined to do anything but stare down at Sam's cock peeking out of his panties.

"Are you going to come for me, Sammy?" Dean asks, and Sam slams his head back, hard enough into Cas to get a grunt. "That's it, Sam, be a good boy, come on my cock."

Cas comes at that, small breathy sounds right in Sam's ear, hot come on his back, and he was so close before that it tips him over the edge. He hears a moan that he knows must be him, though he can't feel himself making the sounds. "Dean," he breathes, and Dean follows suit, coming with a choked off cry. "That's a good boy, Sam," Cas whispers in his ear, and Dean crumples onto him, a heavy weight pressing his legs uncomfortably open, but Sam's not complaining. Sam's never complaining again.

Cas shifts a little to the side, still letting Sam half-lean back on him, but bringing his leg up next to Sam's rib cage. He pets Sam's hair and hums, pressing a kiss into Sam's neck. "You are magnificent, Sam."

"My beautiful boy," Dean says, shifting sideways so he's not crushing them both, his head resting on Sam's shoulder and his left leg still entwined with both of Sam's. He throws an arm across Sam, his hand cupping Sam's ruffle-enclosed hip. "So pretty."

Sam closes his eyes and lets himself bask in their attention. For just a moment, he can almost believe them.


End file.
